Pete Holmes Talks to Gary Gulman About Stand-up, Riffing, and Reusing Material

Gary Gulman, left, and Pete Holmes. Photo-Illustration: Kelly Chiello and Photos by Getty Images

Gary Gulman's new stand-up special, which premiered on Netflix earlier this month, is called It's About Time. Fitting, as Gulman isn't afraid to take his time between specials. Ever since Louis C.K. set this impossible standard of a new special every year, many stand-ups have been trying to put out new material at a more frequent pace. Gulman isn't like that. Four years since his last special, Gulman is as deliberate and exact as he always been. 

Vulture got Pete Holmes, host of the You Made It Weird podcast, creator of the in-production, Judd Apatow-produced HBO show Crashing, and Gary Gulman fan to talk to the comedian about the special and doing stand-up after a special. They also touch on signs from God and reusing material. Enjoy!

Pete Holmes: I think we should start with how good you look. 
Gary Gulman: [Laughs.

What are you doing? Are you like happy in your life? 
No, I'm a mess. Fretting's going on. There's a lot anxiety going on. 

Why? You're Gary Gulman. You're killin' it. What if somebody could, like, teleport into your body, do you think they would have more fun being you? 
Oh my God, yeah. Yeah. 

They would have a great time taking Gulman for a spin. 
Yeah. But I look that way at you. What you've been able to create over these years. I'm like, I would like to hang out in a Pete Holmes suit. 

We could swap. I would like to have your brain. 
I recently re-listened to your interview with Garry Shandling, and you seemed to be in a place where you enjoyed being you. You kept bringing Ram Dass up, and I was like, The next Barnes & Noble that I walk by, I'm getting it

Well, don't wait for God to give you a sign to go to a Barnes & Noble — there's like four of them left. You should take the iTunes store existing as a sign. 
How did you know that I looked for signs from God? Have you ever looked for a sign? I've gotten a sign. 

That's interesting. I am one of those people that tend to string together serendipities. People always say I have a confirmation bias, and I do — I want my beliefs to be true, and I reverse engineer how they're true. I'm one of those people that if I do a load of laundry and then I dump the dry clothes on my bed and there are two socks together, after that whole journey they went in together and they came out together, I'm not kidding, I will go, There's a God.
Oh my gosh. 

So you look for signs.
The best sign I ever got came when I prayed for a sign about if I should leave the football team my freshman year. We were playing in the spring game, which was culmination of all the awful spring practices, which are the most competitive of all the practices. And I missed a block, and the quarterback, who was a golden boy, got creamed. Just crushed. Now, this wasn't the sign. The sign was that the coach — who really spent about five months recruiting you and then you don't hear from him until you graduate pretty much — came storming across the field with smoke coming out of his ears. I was like half in tears but half like, Oh God, this was the sign I was looking for. This couldn't be clearer. I need to get out of this

You got a terrible sign. 
The game was on a Saturday, and Monday I went into his office and I quit. And they tried to convince me to stay and I was like, "No, you don't understand. Take my scholarship back, please." 

I remember the first time I saw you perform. It was you and Bill Burr at the Comedy Connection in Boston, and you were wearing a Harvard sweatshirt. I swear I could almost perfectly recite your set.

I was so young and stand-up was so new and magic to me. You went up and it was a holiday, so there were Christmas lights on the stage. It's this principle that I've since stolen, not just from you: You do a joke up top that isn't good on purpose, to show the audience that you're not there to dance for them. Comedy hates effort. You went out and you we like, "It's nice to see that they decorated for Hanukkah." It got a laugh. And you were like, "Am I saying that right? Hanukkah? Hanukkah?" It was very similar to your milk bit which you did that night. Everyone else was dirty and you went up and you were the funniest and the smartest. All three of my friends were like, "What the fuck was that?" And it was just some random Thursday. You changed our lives. Isn't it weird? We still say, "Hanukkah.  Am I saying that right?" After, I made the mistake that a lot of audience members make where I overly gush to you and then threw Bill Burr a "You were good, too."
Oh gosh! You know that old joke about the three comedians who go to heaven? God meets you at the door and it's the headliner, the middler, and the opener. And they all died in a car crash. And God says to the headliner, "You were fantastic. You weren't a great father and you weren't a great husband, but you made so many people happy and you made them forget about their problems. Come on in." And then he gets to the middler and he says, "A few more years, you probably would have had your own TV show. You were every bit as good as the headliner. You were a horrible person, you cheated on girlfriends, but you made a lot of people happy. Come on in." And then he gets to the opener and he says, "You were good, too." 

Oh, my God.  That is the most stand-up stand-up joke I've ever heard. Since I saw you at the Comedy Connection, you haven't really changed, in a good way. You found your voice early. You still do Gary Gulman humor.
Yeah, I don't feel that I've changed. Like did you see that article in the New York Times about happy comedy. I'm surprised they didn't interview us. 

My first thought was ...
They don't have my number?   

When I first watched you, I noticed how you weren't angry about everything and you weren't bitter. And I always felt like there were so many comedians when they first start, especially in Boston, who are just ranting and getting angry. I'm much sweeter than them. I know a lot of guys are legitimately angry people, and that's fine, but hating things is also a cheap shortcut to having a personality. We all know that in third grade you're like, "Mrs. Nelson sucks," and everyone likes that kid?
I was always the Nelson defender.  

We're Nelson defenders. That's just the beginning of what it feels like to have a perspective. It's easy to say The Hobbit was too long. What did you like about The Hobbit? What was interesting? What was funny about it? That's where you get trolling. What's your problem? We gave you a microphone and you're just like, "movies suck."
Also, if you do that, then they want to hear what else you hate. Then you come across something that you actually enjoy, and you can't extoll the virtues of it. You painted yourself into a corner.

How long have you been doing it?
Over 20 years. 

Yeah, I'm 15 or 16 years. Which is crazy. The thing that I hated most about comedy is when people reflect back to the audience what they already know. So people go up and talking about sex is good. "Don't you like fucking?" This is what you do: make them think about something they haven't. And that's what Seinfeld did. 
One of my favorite things that Seinfeld said is, "A great comedian can occupy a space in people's mind." I also think comedians should riff more. We get so in tune to the next set and the next special. A riff is the best of us.

It's the most present of us. You and I both have that. Though, I also think you should work on your shit. I don't think you should get drunk before your set. I don't think you should get high before your set.
Not any of that, no.

I was talking to T.J. Miller, who riffs a lot, and I told him how I was headlining and I riffed like 60 percent of the time. Then comedy conservative me was like, "What a waste. I didn't record it. I'll never remember it." And he goes, "That one was just for them. It was just for that audience." Sometimes it's just about being right there and doing the show that they need in that moment.
Yeah, that really is a great gift to them. I've been asking every headlining comedian that I've run into lately because my special just came out, so I'm playing audiences that I assume have seen it. How much new stuff are they expecting? Do they want to hear the hits? Are there gonna be requests at the end? The last time I went out with a new hour there were. And even at my new special, they were like, "Hey, do the grapefruit joke," and I was like, "Well, we're spending a lot of money to record new stuff, I can't really record this old stuff.  

I just taped my special, and at the end I did a little bit. But you already know the request, for me it's my magic bit or Pierce. It's a nice way to let them know it's okay if they want to hear something from me. You do new stuff and then you say, "I'm about to wrap up, is there anything you wish I did?"
For people who have seen the special, I'll have 45 minutes. But I know there are some people. One time, I did something I had done on Conan and one person said to the guy who owns the place, "Ah, I've seen that." Because Louis C.K. and Patton Oswalt said if they see anything good on television, and that includes their Saturday Night Live appearances and their late night appearances, they're not coming back. 

It's even more haunting, the Patton quote is, "You can go and do old stuff and they won't complain, they'll like it, but they won't come next time you're in town." I disagree. It's a little big touchy to disagree with greats and maybe time will show that they're right, but if you're coming to see my material, then I have to view these people as fans. I always have new jokes, but you're going for that feel, and you have this, which is we're going to see our friend Gary. And that's why I like to riff, that's why I like to do old stuff. You tell them, you know, it's old. 

Audiences are getting more sophisticated. And really the compliment I'd like to give you is you have that musical comedy. I like hearing "Born in the USA" again and I like hearing Grapefruit again. The audience and I are doing it together. I've also fucked before. So how is this fuck going to be different? Still my dick. It's still the magic bit. But what's it going to feel like once we do it? If I feel them backing away in the middle of an old bit, I'll go, "Don't back away, I've heard it before too." We're not robots. We're trying to create something with them, not at them. The ship is leaving the dock, and if you run now, you can jump on, but this is the last call to get in on the joy. I like that much more than trying to win them over. That's what I tell new stand-ups. Did you read Jay Sankey's book? 
Is that the zen? 

Zen and the Art of Stand-Up Comedy.
I did read it. I wanna reread it because I remember I got a lot out of it. I rarely get a lot out of those.

But it says, "Ask yourself, when would you laugh?"
Do you find that there's some part of you now where you'd look like a lunatic if you were laughing out loud while writing? 

At your own jokes?
Yeah. For the most part I'm like, that's something that will get a laugh. That's a clever twist. That'll get a laugh rather than me actually laughing at it. 

I do laugh at my own jokes a lot onstage. We're all there to be in the space where we're trying just for one fucking hour of our day to stop being so discriminating and stop being so adult and so critical and lighten the fuck up. I'm trying to do that too.
I always feel I wanna laugh and then, this is really bad, I think, But what will the other comedians say? It's a joy problem. I create this mean comedian who's gonna say something. 

I used to picture a back table where it was Mitch Hedberg and Dave Attell and all these people that were gonna heckle me: "Hack!"
Meanwhile, those guys are the nicest guys. I've never seen them running anybody down. 

And if they do, who cares? I know how someone might make fun of me. "Oh Pete, and he does this."
I do that too. All the words that rhyme with Gary; talks about coffee for four hours. I'm sorry, I'm stuck in here. This is what I do. This is the sort of stuff my brain does. There was a guy who did an impression of me, and in the background there was one of those time-lapse clocks that went around and around, and I'd be still talking about the same thing. 

I saw that.
It was so funny, but also sweet. Once you get to a certain place where you are so clearly a thing that then we run into the third-grade people that go, "That sucks and it's easy." But what's weird is you were you the whole time. 

But do you think you were more you back then then you are now? Do you think some of it has been chipped away?
Maybe. That's an interesting question. Because when I think back on that night when you saw me, I know that my mindset was different back then. Every set meant something and now every set is just contributing to developing the next. Not every night do I have that night where you said, "That was for them." I feel like back then, it was mostly just me being me and it was pure. 

Yeah, I taped my special a few weeks ago, and I haven't gone up since because I just don't feel like it. Sometimes I do it for Younger Peter. Younger Pete would be like, "You could call in your avails at the Comedy Cellar and you're not doing it?" And I'm like, "You'll get it. You'll get it later." 
When did you record your previous special? 

There was two years in between.
So you haven't been doing the material for that long. My specials were four years apart and I couldn't wait to get onstage and do something that I hadn't done.

That's what I should be doing. Now I can go up and start new which is a good feeling. 
That is a good feeling. But I'm at a point now where I'm nine months in and there's about 30 minutes there. Have you ever dealt with writer's block?

I'm real loose with myself. I'm a gentle boss. And I'm a big believer in everything is writing. I'm talking to you right now and this is writing. And I watch TV and that's writing. I sleep and that's writing.
Well, I think that's the right way to be.

What is gained by trying to be hard on yourself?
I am abusive to myself about not producing. 

I'll tell you that it goes back to the vacationing in your own body. You're Gary Gulman and you're a great comedian.
It doesn't bother you about Gary Gulman that Gary Gulman is not a household name. Sometimes I look at me as how the meanest tabloid journalist would write about the journey of Gary Gulman. "Gary Gulman had some development deals in the early 2000s and we didn't really hear from him that much. He was sort of a ne'er do well, but he never really reached his potential as a comedian." That's the way I look at myself, like what's the worst thing people could say about me? I'm worried that's the way I'm being looked at, so I guess this is more therapy right now. 

I would not take anything personally. You are a great comedian. And who knows what can happen? It's not that speech. The speech that I want to give you is that people should copy your process. It's not that you should do an hour every year like Louis. You write the Gary Gulman-iest jokes, and of all the Gary Gulmans, you are the most Gary Gulman. And you're developing and you're putting out specials and you are making the comedy that we wanna see. Conan told me a great thing. He said, "All you do is you keep ringing your bell." Everything else in show business is changing its sound — farting, a donkey going "eeaww" — and you're just in the corner hitting this cowbell. I hear you being like, "Well, I have my development deal," but you just keep hitting the bell. In all the commotion, after a while, a couple more people will go, "I've been hearing that bell. What the fuck is that bell?" I do this a lot where I love my friends more than they love themselves, but it's like, if you could see you how I see you, you would be like, "This is great and everything's going to be fine."